Here’s what they have cooked up now.
Former President Barack Obama and late-night host Jimmy Kimmel have once again found themselves on the same side of America’s political divide, using a new HBO comedy series to take aim at President Donald Trump.
Kimmel appeared in the July 3 episode of Larry David’s new HBO satire, Life, Larry and the Pursuit of Unhappiness: An Almost History of America. The series is executive produced by Barack Obama and former First Lady Michelle Obama and uses fictional historical scenes to comment on modern American politics.
Although President Trump is never mentioned by name, the episode includes several jokes and references that many viewers interpreted as directed at the current administration.
One of the show’s featured moments includes a posthumous appearance by filmmaker and longtime Trump critic Rob Reiner, who portrays George Washington. In the sketch, Washington explains why he chose not to seek a third presidential term and argues that peaceful transfers of power are essential to protecting the Constitution.
Larry David, dressed in colonial clothing, then raises hypothetical questions about what could happen if a future president ignored constitutional limits or used the office to silence critics.
As the conversation unfolds, Jimmy Kimmel appears as a member of the crowd, sarcastically dismissing the possibility before joking that no president would ever spend time responding to comedians or people who make fun of him.
The exchange was widely viewed as another indirect jab at President Trump, continuing Kimmel’s years-long pattern of criticizing the Republican leader during television appearances and on his ABC late-night program.
Kimmel has increasingly blended comedy with political commentary in recent years, making President Trump a frequent subject of his opening monologues. His remarks have often generated strong reactions from both supporters and critics.
Earlier this year, Kimmel faced backlash after making a joke involving First Lady Melania Trump that many conservatives considered inappropriate. The comments quickly spread across social media and fueled renewed criticism of the comedian’s increasingly political style.
President Trump has repeatedly responded to Kimmel’s remarks, criticizing the comedian’s performance and urging ABC to replace him. In an April social media post, Trump questioned why the network continued to employ Kimmel and argued that viewers had grown tired of his political humor.
Kimmel has also been involved in several controversies over politically charged comments in recent years. Despite criticism from conservative audiences, ABC has continued to support the late-night host.
The HBO series marks another high-profile collaboration between Hollywood entertainment figures and the Obamas, reinforcing what many conservatives see as the close relationship between the entertainment industry and Democratic political leaders.
For supporters of President Trump, the latest episode is likely to be viewed as another example of major media and entertainment personalities using comedy programming to criticize the president. Supporters of the show, meanwhile, argue that political satire has long been part of American television and remains a form of free expression.
As the 2026 political season continues to heat up, the intersection of entertainment and politics is expected to remain a major flashpoint, with figures like Jimmy Kimmel, Larry David, Barack Obama, and President Donald Trump continuing to dominate headlines both on television and online.